Dimethyl Sulfoxide → 5-{9-(Cyclopropylmethyl)-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

HRID 421399

反応式

HRID 421399 の反応式
CS(C)=O.Cl[C:6]1[N:7]([CH2:28][CH:29]2[CH2:31][CH2:30]2)[C:8]2[C:13]([N:14]=1)=[C:12]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[N:11]=[C:10]([C:21]1[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=1)[N:9]=2.[CH3:32][C@H:33]1[CH2:38][NH:37][CH2:36][CH2:35][NH:34]1>C(Cl)Cl.CO>[CH:29]1([CH2:28][N:7]2[C:6]([N:37]3[CH2:36][CH2:35][NH:34][C@@H:33]([CH3:32])[CH2:38]3)=[N:14][C:13]3[C:8]2=[N:9][C:10]([C:21]2[CH:22]=[N:23][C:24]([NH2:27])=[N:25][CH:26]=2)=[N:11][C:12]=3[N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:31][CH2:30]1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 27342192-Methylpiperazine, (S)-2 回HCID 593335195-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine

生成物 1

HCID 593335285-{9-(Cyclopropylmethyl)-8-[(3S)-3-methylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine収率 93.1%

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

反応条件

温度
85 °C

実験手順

A dimethyl sulfoxide suspension (5 ml) of 5-[8-chloro-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl]pyrimidin-2-amine (476.1 mg, 1.23 mmol) and (2S)-2-methylpiperazine (616.4 mg, 6.15 mmol) was heated at 100° C. to dissolve and the resulting mixture was stirred at 85° C. for 18.5 hours. (2S)-2-Methylpiperazine (123.3 mg, 1.23 mmol) was added and the resulting mixture was further stirred at 85° C. for 5.5 hours, left standing to cool, poured into methylene chloride-methanol (10:1), and washed with saturated aqueous sodium hydrogen carbonate solution. The organic layer was dried over anhydrous sodium sulfate, the mixture was filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=32:1 to 9:1) to give the title compound (516.0 mg, 93%) as a pale yellow solid.

後処理

  1. dissolutionto dissolve
  2. stirringthe resulting mixture was further stirred at 85° C. for 5.5 hours
  3. waitleft
  4. temperatureto cool
  5. washwashed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationthe mixture was filtrated
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customthe resulting residue was purified by medium pressure silica gel column chromatography (methylene chloride:methanol=32:1 to 9:1)

出典と根拠

ORDレコード
ord-28aa3808aaae4469862e75b960b0740b
出典データセット
uspto-grants-2012_01
特許番号
US08097622B2

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